EP0688773A1 - 2-Phényl-7-chloro-perhydroimidazo(1,5a)pyridines - Google Patents

2-Phényl-7-chloro-perhydroimidazo(1,5a)pyridines Download PDF

Info

Publication number: EP0688773A1
Authority: EP; European Patent Office
Prior art keywords: 4alkyl; substituted; halogen; 4alkoxy; chloro
Prior art date: 1994-06-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP95810410A

Other languages

German (de)

English (en)

Other versions

EP0688773B1 (fr

Inventor

Karl Seckinger

Sasank Sekhar Mohanty

Karlheinz Milzner

Fred Kuhnen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Sandoz AG

Original Assignee

Sandoz Erfindungen Verwaltungs GmbH

Novartis AG

Sandoz AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-06-23

Filing date

1995-06-20

Publication date

1995-12-27

1995-06-20 Application filed by Sandoz Erfindungen Verwaltungs GmbH, Novartis AG, Sandoz AG filed Critical Sandoz Erfindungen Verwaltungs GmbH

1995-12-27 Publication of EP0688773A1 publication Critical patent/EP0688773A1/fr

1998-05-20 Application granted granted Critical

1998-05-20 Publication of EP0688773B1 publication Critical patent/EP0688773B1/fr

2015-06-20 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000003222 pyridines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 63
229910052736 halogen Inorganic materials 0.000 claims abstract description 22
150000002367 halogens Chemical group 0.000 claims abstract description 22
239000000203 mixture Substances 0.000 claims abstract description 20
-1 2-oxo-3-tetrahydrofuranyl Chemical group 0.000 claims abstract description 17
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 15
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 13
229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
239000000460 chlorine Chemical group 0.000 claims abstract description 12
229910052731 fluorine Chemical group 0.000 claims abstract description 12
239000011737 fluorine Chemical group 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052717 sulfur Chemical group 0.000 claims abstract description 5
239000011593 sulfur Chemical group 0.000 claims abstract description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims abstract description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
125000000466 oxiranyl group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical group 0.000 claims abstract 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
241000196324 Embryophyta Species 0.000 claims description 27
230000002363 herbicidal effect Effects 0.000 claims description 17
238000000034 method Methods 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229940114081 cinnamate Drugs 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
239000004480 active ingredient Substances 0.000 description 7
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
241000209140 Triticum Species 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
238000009472 formulation Methods 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
235000009973 maize Nutrition 0.000 description 5
238000002156 mixing Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000428 dust Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
0 C*1*C(CC(CC2)N)*2**1 Chemical compound C*1*C(CC(CC2)N)*2**1 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000020551 Helianthus annuus Species 0.000 description 2
235000003222 Helianthus annuus Nutrition 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
244000082988 Secale cereale Species 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
240000000359 Triticum dicoccon Species 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
244000038559 crop plants Species 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
MMUFKGAMEFAMSM-UHFFFAOYSA-N 7-fluoro-2,3,3a,4,5,6,7,7a-octahydro-1h-imidazo[4,5-b]pyridine Chemical class FC1CCNC2NCNC12 MMUFKGAMEFAMSM-UHFFFAOYSA-N 0.000 description 1
240000006995 Abutilon theophrasti Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
240000005702 Galium aparine Species 0.000 description 1
235000014820 Galium aparine Nutrition 0.000 description 1
244000299507 Gossypium hirsutum Species 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
241000207890 Ipomoea purpurea Species 0.000 description 1
244000042664 Matricaria chamomilla Species 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
244000234609 Portulaca oleracea Species 0.000 description 1
235000001855 Portulaca oleracea Nutrition 0.000 description 1
240000003705 Senecio vulgaris Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
244000061457 Solanum nigrum Species 0.000 description 1
235000002594 Solanum nigrum Nutrition 0.000 description 1
240000003829 Sorghum propinquum Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
244000067505 Xanthium strumarium Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
230000002605 anti-dotal effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
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235000008504 concentrate Nutrition 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000005187 foaming Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
230000035784 germination Effects 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000001469 hydantoins Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
WSFMKTQBYYWDJK-UHFFFAOYSA-N methyl 3-(5-amino-2-chloro-4-fluorophenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC(N)=C(F)C=C1Cl WSFMKTQBYYWDJK-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000008654 plant damage Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
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LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical group C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

EP95810410A 1994-06-23 1995-06-20 2-Phényl-7-chloro-perhydroimidazo(1,5-a)pyridines Expired - Lifetime EP0688773B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9412603		1994-06-23
GB9412603A GB9412603D0 (en)	1994-06-23	1994-06-23	Organic compounds

Publications (2)

Publication Number	Publication Date
EP0688773A1 true EP0688773A1 (fr)	1995-12-27
EP0688773B1 EP0688773B1 (fr)	1998-05-20

Family

ID=10757203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP95810410A Expired - Lifetime EP0688773B1 (fr)	1994-06-23	1995-06-20	2-Phényl-7-chloro-perhydroimidazo(1,5-a)pyridines

Country Status (6)

Country	Link
US (1)	US5665681A (fr)
EP (1)	EP0688773B1 (fr)
JP (1)	JPH0853449A (fr)
DE (1)	DE69502542T2 (fr)
GB (1)	GB9412603D0 (fr)
RU (1)	RU95109881A (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998056790A1 (fr) *	1997-06-11	1998-12-17	Glaxo Group Limited	Dihydroimidazo[1,5-b]isoquinoline-1,3-diones utilises comme inhibiteurs de l'apoproteine b-100
WO2003042191A1 (fr) *	2001-11-12	2003-05-22	Pfizer Products Inc.	Benzamide et heteroarylamide utilises comme antagonistes du recepteur p2x7
US7071223B1 (en)	2002-12-31	2006-07-04	Pfizer, Inc.	Benzamide inhibitors of the P2X7 receptor
US7176202B2 (en)	2002-12-31	2007-02-13	Pfizer Inc.	Benzamide inhibitors of the P2X7 receptor
US7235657B2 (en)	2004-06-29	2007-06-26	Pfizer Inc.	Methods for preparing P2X7 inhibitors
WO2012041789A1 (fr)	2010-10-01	2012-04-05	Basf Se	Benzoxazinones herbicides

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH1087663A (ja) *	1996-09-12	1998-04-07	Sagami Chem Res Center	双環性ヒダントイン誘導体、それらの製造方法およびそれらを有効成分とする除草剤
US6573218B1 (en)	1998-09-09	2003-06-03	Ishihara Sangyo Kaisha, Ltd.	Fused-benzene derivatives useful as herbicides
MXPA02006134A (es)	1999-12-21	2002-12-13	Guilford Pharm Inc	Compuestos derivados de hidantoina, composiciones farmaceuticas y metodos de uso de los mismos.
DE10307142A1 (de) *	2003-02-20	2004-09-02	Bayer Cropscience Ag	Substituierte N-Aryl-Stickstoffheterocyclen
CN101616908B (zh)	2006-12-29	2014-09-10	Abbvie德国有限责任两合公司	羧酰胺化合物及它们作为钙蛋白酶抑制剂的用途
JP5711738B2 (ja) *	2009-07-21	2015-05-07	マローネバイオイノベーションズ，インコーポレイテッド	植物有害生物を防除するためのサルメンチンおよびその類似体の使用
WO2015050705A1 (fr)	2013-10-01	2015-04-09	Marrone Bio Innovations, Inc.	Utilisation de sarmentine et de ses analogues avec un herbicide et compositions associées
AU2018307564B2 (en) *	2017-07-24	2022-05-05	Redag Crop Protection Ltd.	Benzoxazinone derivatives useful as herbicides
CN109896973B (zh) *	2019-02-22	2021-12-24	中国热带农业科学院热带生物技术研究所	一种肉桂酰胺衍生物及其用途
CN119613399B (zh) *	2023-09-14	2025-12-09	江西天宇化工有限公司	一种含有烷氧乙酸酯取代基的四取代苯甲酸酯类化合物及其应用

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EP0384973A2 (fr) *	1989-03-02	1990-09-05	Agro-Kanesho Co., Ltd.	Composés hétérocycliques, procédés pour leur préparation et compositions herbicides les contenant comme composants actifs
EP0468924A2 (fr) *	1990-07-23	1992-01-29	Ciba-Geigy Ag	Nouveaux herbicides
EP0493323A1 (fr)	1990-12-18	1992-07-01	Sandoz Ltd.	Composés d'hydantoine

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DK156573C (da) *	1981-06-16	1990-01-29	Sumitomo Chemical Co	2-(2-fluor-4-halogen-5-substitueret-phenyl)-hydantoinderivater, et herbicidt praeparat indeholdende disse, en fremgangsmaade til bekaempelse af ukrudt under anvendelse af disse samt anvendelse af disse som herbicid

1994
- 1994-06-23 GB GB9412603A patent/GB9412603D0/en active Pending
1995
- 1995-06-20 EP EP95810410A patent/EP0688773B1/fr not_active Expired - Lifetime
- 1995-06-20 US US08/492,687 patent/US5665681A/en not_active Expired - Fee Related
- 1995-06-20 DE DE69502542T patent/DE69502542T2/de not_active Expired - Fee Related
- 1995-06-21 JP JP7154600A patent/JPH0853449A/ja active Pending
- 1995-06-21 RU RU95109881/04A patent/RU95109881A/ru unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0384973A2 (fr) *	1989-03-02	1990-09-05	Agro-Kanesho Co., Ltd.	Composés hétérocycliques, procédés pour leur préparation et compositions herbicides les contenant comme composants actifs
EP0468924A2 (fr) *	1990-07-23	1992-01-29	Ciba-Geigy Ag	Nouveaux herbicides
EP0493323A1 (fr)	1990-12-18	1992-07-01	Sandoz Ltd.	Composés d'hydantoine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TETRAHEDRON, vol. 47, no. 24, 1991, pages 4039 - 4062

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998056790A1 (fr) *	1997-06-11	1998-12-17	Glaxo Group Limited	Dihydroimidazo[1,5-b]isoquinoline-1,3-diones utilises comme inhibiteurs de l'apoproteine b-100
WO2003042191A1 (fr) *	2001-11-12	2003-05-22	Pfizer Products Inc.	Benzamide et heteroarylamide utilises comme antagonistes du recepteur p2x7
US7214677B2 (en)	2001-11-12	2007-05-08	Pfizer Inc.	Benzamide, heteroarylamide and reverse amides
US7235549B2 (en)	2001-11-12	2007-06-26	Pfizer Inc.	Benzamide, heteroarylamide and reverse amides
US7071223B1 (en)	2002-12-31	2006-07-04	Pfizer, Inc.	Benzamide inhibitors of the P2X7 receptor
US7176202B2 (en)	2002-12-31	2007-02-13	Pfizer Inc.	Benzamide inhibitors of the P2X7 receptor
US7407956B2 (en)	2002-12-31	2008-08-05	Pfizer, Inc.	Benzamide inhibitors of the P2X7 receptor
US7235657B2 (en)	2004-06-29	2007-06-26	Pfizer Inc.	Methods for preparing P2X7 inhibitors
WO2012041789A1 (fr)	2010-10-01	2012-04-05	Basf Se	Benzoxazinones herbicides

Also Published As

Publication number	Publication date
EP0688773B1 (fr)	1998-05-20
GB9412603D0 (en)	1994-08-10
DE69502542D1 (de)	1998-06-25
DE69502542T2 (de)	1999-01-21
US5665681A (en)	1997-09-09
RU95109881A (ru)	1997-04-20
JPH0853449A (ja)	1996-02-27

Publication	Publication Date	Title
EP0688773B1 (fr)	1998-05-20	2-Phényl-7-chloro-perhydroimidazo(1,5-a)pyridines
SU1665875A3 (ru)	1991-07-23	Способ получени Е-изомеров производных акриловой кислоты
US5438033A (en)	1995-08-01	Substituted pyridine herbicides
EP0493323A1 (fr)	1992-07-01	Composés d'hydantoine
JP2002528447A (ja)	2002-09-03	殺虫性１−（置換ピリジル）−１，２，４−トリアゾール
US5332717A (en)	1994-07-26	Heterocyclic compounds
US4614535A (en)	1986-09-30	Herbicidal imidazolinones
US5633218A (en)	1997-05-27	Herbicidal benzodioxoles and benzodioxanes
JP2615228B2 (ja)	1997-05-28	フルオロエトキシアミノトリアジン
RU2054871C1 (ru)	1996-02-27	Гербицидное средство и способ борьбы с сорняками
CZ280644B6 (cs)	1996-03-13	Herbicidní prostředek
EP0468930A1 (fr)	1992-01-29	Composés arylaminocarbonyliques
US4721522A (en)	1988-01-26	1H-Imidazo [1',2':1,2]pyrrolo[3,4-b]pyridines and their use as herbicidal agents
EP0527016A1 (fr)	1993-02-10	Quinoxalinyloxyéthers herbicides
US4741767A (en)	1988-05-03	2H-Imidazo(1',2':1,2)pyrrolo(3,4-B)pyridine compounds, and their use as herbicidal agents
JPS62138476A (ja)	1987-06-22	５−フルオルアシルアミノ−４−ニトロ−１−アリ−ル−ピラゾ−ル類
US4304791A (en)	1981-12-08	Benzenamines, formulations, and fungicidal method
KR910006448B1 (ko)	1991-08-26	복소환 화합물, 그의 제조방법 및 그를 유효성분으로서 함유하는 제초제 조성물
EP0427445B1 (fr)	1994-06-08	Dérivés amidés d'acides benzylidène-aminooxyalcane(thi)oiques, procédé pour leur préparation et herbicides
US6232271B1 (en)	2001-05-15	1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio- substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides
US4722749A (en)	1988-02-02	Pyridinesulfonamides and their use as herbicidal agents
DE3633485A1 (de)	1988-04-07	Substituierte 2-pyri(mi)dyl-2'-pyridyl-(thio)-ether
EP0514339A1 (fr)	1992-11-19	Composés arylaminocarbonyliques
US5376620A (en)	1994-12-27	Sulfonamide derivative, process for preparing the same and herbicide using the same
DE4009761A1 (de)	1991-01-31	2h-pyridazinon-derivate

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